1. Field of the Invention
Several vegetable oils produced mainly for edible use also find industrial applications. For example, soybean oil can be converted into alkyd resins for protective coatings, plasticizers, dimer acids, surfactants, and other products. Oleic acid is one of the most common fatty acids in vegetable oils. This invention relates to the fermentative conversion of oleic acid into a multifunctional, long-chain aliphatic acid with potential utility as a plasticizer and as a source of intermediates in the synthesis of specialty chemicals.
2. Description of the Prior Art
Several microbial/enzymic approaches for modifying agricultural oils or fats have been reported in recent years, including commercial application of lipases for fat splitting Brockerhoff et al., In Lipolytic Enzymes, Academic Press, New York (1974)!. Nocardia corallina, Pseudomonas sp., and Puccinia graminis are known to biosynthesize epoxy groups Furuhashi et al., Eur. J. Appl. Microbiol. Biotechnol. 12: 39-45 (1981); Nihaus et al., J. Am. Chem. Soc. 89: 4227 (1967); Powell et al., Lipids 2: 172 (1967)!. Oleic acid serves as substrate for Pseudomonas and P. graminis to form 9,1-epoxy stearic acid. The cytochrome p-450 system from Bacillus megatherium appears to serve as a common enzyme for both epoxidation and hydroxylation of a variety of monounsaturated fatty acids Ruettinger et al., J. Biol. Chem. 256: 5728-5734 (1981)!. Marsh et al., Biochem. Biophys. Acta 60: 32 (1962)! show that yeast biosynthesizes hydroxy stearic acid from stearic acid. Microbial conersion of oleic acid to 10-hydroxystearic acid has been reported by Wallen et al. Arch. Biochem. Biophys. 99: 249-253 (1962)!. They teach that a Pseudomoned isolated frcm a fatty material hydrates oleic acid at the double bond with a 14% yield. Litchfield et al. (U.S. Pat. No. 4,582,804) disclose that Rhodococcus rhodochrous converts oleic acid to 10-hydroxystearate and minor amounts of 10-keto-stearic acid. Kritala et al. Appl. Microbiol. Biotechnol. 32:299-304 (1989)! have identified several microorganisms that hydrate oleic acid to 10-hydroxystearic acid at greater than 90% yield.